10,771

Oakland, MD Homes

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  • /52

    $399,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,780 Sq Ft

    2254 Garrett Rd, Oakland, MD 21550

    Situated on an expansive and private 17 acres of property this Southern Garrett county home offers its new owners the unique opportunity of space and privacy all while being close to town and additional amenities. A private paved driveway leads you to an extensively updated and lovingly maintained home that has a spacious feeling 3 bedrooms and 2 full bathrooms on the main floor. A full basement

    Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    2254 Garrett Rd, Oakland, MD 21550
  • /47

    $270,000

    Sold Jun 20, 2025

    403 O St, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 2,240 Sq Ft
    • Built 1976

    Last Sold Summary

    • $121/SF
    • 329 Days On Market

    Current Estimated Value $262,327

    Last Listing Agent ANGELA BOSLEY Taylor-Made Deep Creek Real Estate, LLC

    403 O St, Oakland, MD 21550
    • /73

      Est $236,275

      Not Listed For Sale

      723 E Alder St, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,764 Sq Ft
      • Built 1950
      723 E Alder St, Oakland, MD 21550

      Last Sold Summary

  • /12

    $39,000

    • Land
    • 1.02 Acres
    • $38,235 per Acre

    Lot 14 Warnick Way, Oakland, MD 21550

    Enjoy scenic mountain views from this 1.02 acre mostly wooded homesite. This property offers a peaceful setting with convenient access off Spring Glade Road and is ideally located between Oakland and Deep Creek Lake. No HOA and mobile homes are not permitted, helping maintain the character of the area. Do not miss this great opportunity to build your getaway or full time residence. Contact me

    Nicole Jackson Railey Realty, Inc.

    Lot 14 Warnick Way, Oakland, MD 21550
  • /47

    $260,000

    Sold Feb 27, 2026

    20160 Garrett Hwy Unit H708, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft
    • Built 1972

    Last Sold Summary

    • $473/SF
    • 234 Days On Market

    Current Estimated Value $262,544

    Last Listing Agent Charlotte Savoy The KW Collective

    20160 Garrett Hwy Unit H708, Oakland, MD 21550
    • /130

      Est $1,087,919

      Not Listed For Sale

      943 S Blakeslee Rd, Oakland, MD 21550

      • 4 Beds
      • 4 Baths
      • 3,426 Sq Ft
      • Built 1990
      943 S Blakeslee Rd, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • /24

    $18,000

    • Land
    • 26,136 Sq Ft
    • $30,000 per Acre

    22 Elm Dr, Oakland, MD 21550

    Build your dream getaway in the gated community of Youghiogheny Mountain Resort! This flat 0.60-acre lot offers an ideal setting for easy building. Perfect for a full-time home or weekend retreat. Enjoy miles of ATV trails, hunting, and fishing, all while being just minutes from Wisp Resort, Deep Creek Lake, and Swallow Falls State Park. Approved for a sand mound septic system and located within

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    22 Elm Dr, Oakland, MD 21550
  • /107

    $1,350,000

    Sold Sep 19, 2025

    421 Penn Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 4,284 Sq Ft
    • Built 1986

    Last Sold Summary

    • $315/SF
    • 54 Days On Market

    Current Estimated Value $1,425,284

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    421 Penn Cove Rd, Oakland, MD 21550
    • /88

      Est $374,566

      Not Listed For Sale

      223 N 2nd St, Oakland, MD 21550

      • 5 Beds
      • 4 Baths
      • 3,120 Sq Ft
      • Built 1920
      223 N 2nd St, Oakland, MD 21550

      Last Sold Summary

      • 109 Days On Market

  • /30

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 3,278 Sq Ft

    267 San Francisco St, Oakland, MD 21550

    Welcome to your secluded Deep Creek retreat! This stunning property offers expansive lake views! So clear you’ll catch the slopes of Wisp in the distance. Includes 3 lots and the privacy is unmatched. This house was torn down to the foundation and a new house was built in 2009. Inside, you’ll find four spacious bedrooms, two and a half baths, and soaring vaulted ceilings and a grand fireplace.

    Bradley West HomeSmart

    267 San Francisco St, Oakland, MD 21550
  • /61

    $820,000

    Sold Sep 02, 2025

    939 Glendale Rd, Oakland, MD 21550

    • 3 Beds
    • 3 Baths
    • Built 1990

    Last Sold Summary

    • 18 Days On Market

    Current Estimated Value $822,708

    Last Listing Agent Sean Sober Taylor-Made Deep Creek Real Estate, LLC

    939 Glendale Rd, Oakland, MD 21550
    • /29

      Not Listed For Sale

      22 Black Oak Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1998
      22 Black Oak Dr, Oakland, MD 21550

      Last Sold Summary

      • 16 Days On Market

  • /50

    $339,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    961 Cedar Ln, Oakland, MD 21550

    Tucked away in the woods on 1.72 acres, this stunning 4-bedroom, 2.5-bath mountain retreat offers privacy, comfort, and plenty of space to unwind. Step inside to find a warm and inviting main level highlighted by a stone fireplace, cozy dining area, and galley-style kitchen. Relax on the screened-in porch complete with a hot tub under roof, perfect for year-round enjoyment. The finished basement

    Laura Newhall Taylor-Made Deep Creek Real Estate, LLC

    961 Cedar Ln, Oakland, MD 21550
  • /100

    $1,860,000

    Sold Oct 06, 2025

    237 Glendale Rd, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 3,735 Sq Ft
    • Built 2002

    Last Sold Summary

    • $498/SF
    • 88 Days On Market

    Current Estimated Value $1,868,816

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    237 Glendale Rd, Oakland, MD 21550
    • /54

      Est $2,394,960

      Not Listed For Sale

      375 Glendale Rd, Oakland, MD 21550

      • 8 Beds
      • 6.5 Baths
      • 5,638 Sq Ft
      • Built 2001
      375 Glendale Rd, Oakland, MD 21550

      Last Sold Summary

      • 134 Days On Market

  • /47

    $569,000

    $20K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550

    Tucked into a peaceful, wooded setting yet right in the heart of everything Deep Creek Lake has to offer, Whispering Pines is the ultimate turnkey mountain retreat. This impeccably maintained 5-bedroom townhome spans three levels of inviting living space and features an attached garage—perfect for hosting family, friends, or guests year-round. Enjoy the best of both worlds: a private, serene

    Nina Beitzel Railey Realty, Inc.

    178 Winding Trail Ln Unit 5B, Oakland, MD 21550
  • /56

    $157,000

    Sold Aug 29, 2025

    416 Shenandoah Ave, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • Built 1940

    Last Sold Summary

    • $161/SF
    • 4 Days On Market

    Current Estimated Value $151,815

    Last Listing Agent Rich Orr Railey Realty, Inc.

    416 Shenandoah Ave, Oakland, MD 21550
    • /18

      Est $243,525

      Not Listed For Sale

      9 Laurel Brook Dr, Oakland, MD 21550

      • 2 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1989
      9 Laurel Brook Dr, Oakland, MD 21550

      Last Sold Summary

      • 13 Days On Market

  • /12

    $45,000

    • Land
    • 14,810 Sq Ft
    • $132,353 per Acre

    LOT 181 Santa fe Trail, Oakland, MD 21550

    Don't miss the opportunity to own a lake area lot near the one and only Deep Creek Lake. 0.34 acre wooded lot, close to multiple local attractions. Call today! Verify utilities with Garrett County Environmental Department. Being sold subject to successful perc.

    Amy Skipper Railey Realty, Inc.

    LOT 181 Santa fe Trail, Oakland, MD 21550
  • /51

    $425,000

    Sold Oct 22, 2025

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,202 Sq Ft
    • Built 2012

    Last Sold Summary

    • $193/SF
    • 130 Days On Market

    Current Estimated Value $436,847

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    • /55

      Est $761,542

      Not Listed For Sale

      1557 Mountainview Dr, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,590 Sq Ft
      • Built 1992
      1557 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 163 Days On Market

  • /55

    $359,000

    $20K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,388 Sq Ft

    215 H St, Oakland, MD 21550

    Welcome to the Maggie Watson Cottage, where historic charm meets modern convenience in the heart of Mountain Lake Park. This beautifully renovated home offers 3 bedrooms and 3 full bathrooms, thoughtfully updated to provide today’s comforts while preserving its timeless character. The interior features updated paint, both refinished and brand new hardwood flooring, and a modern gourmet kitchen

    Rachel Bruch Railey Realty, Inc.

    215 H St, Oakland, MD 21550
  • /17

    $118,800

    Under Contract
    • Land
    • 7.33 Acres
    • $16,207 per Acre

    1995 Bethlehem Rd, Oakland, MD 21550

    Thinking of an escape to the Maryland Mountaintop? You can get away to almost 8 acres of pristine woodland, bordering the State Forest. Walk the woodsy trails and take in the flora and fauna or harvest the game you've been dreaming of. Choose this affordable place for an easier start w/well, septic, & electric already in place & a 2 story building to use as is or make your own. Enjoy an even

    Lana Roby The KW Collective

    1995 Bethlehem Rd, Oakland, MD 21550
    • /91

      Est $301,813

      Not Listed For Sale

      106 H St, Oakland, MD 21550

      • 7 Beds
      • 3 Baths
      • 2,934 Sq Ft
      • Built 1900
      106 H St, Oakland, MD 21550

      Last Sold Summary

      • 1,050 Days On Market

  • /4

    $29,900

    • Land
    • 1.09 Acres
    • $27,431 per Acre

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550

    1+ acre building lot. Fairly leveled cleared lot with some distant mountain views. Paved County road frontage with private road/drive access to lot. Approved for private septic and well. Electric on-site. Located approx. 10+ mins from Deep Creek Lake and approx. less than 5 minutes from Oakland. Located within small 8 lot development, "The Homestead".

    Chip Smith 1 Real Estate Source LLC

    0 Garrett Trail Unit MDGA2010758, Oakland, MD 21550
  • /10

    $55,000

    Sold May 25, 2026

    114 C St, Oakland, MD 21550

    • 768 Sq Ft
    • Built 1999

    Last Sold Summary

    • 8% Below List Price
    • $72/SF
    • 60 Days On Market

    Current Estimated Value $59,602

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    114 C St, Oakland, MD 21550
    • /63

      Est $2,564,598

      Not Listed For Sale

      25 Old Chestnut Dr, Oakland, MD 21550

      • 9 Beds
      • 9 Baths
      • 5,362 Sq Ft
      • Built 2003
      25 Old Chestnut Dr, Oakland, MD 21550

      Last Sold Summary

      • 270 Days On Market

  • /80

    $950,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,219 Sq Ft

    208 Cliff Dr, Oakland, MD 21550

    Picture perfect, private and wooded mountain retreat featuring lake access in a prime location close to all area amenities! Seasonal lake views! This highly desirable property offers the opportunity to walk to your dock featuring TWO slips for your use. A two-minute walk at the end of the quiet road leads you to the property's deeded lake-front land and two dock slips. Nestled among the

    Kellyann Green Railey Realty, Inc.

    208 Cliff Dr, Oakland, MD 21550
  • /37

    $365,900

    Sold Mar 23, 2026

    17979 Garrett Hwy, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Above List Price
    • $381/SF
    • 9 Days On Market

    Current Estimated Value $363,153

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    17979 Garrett Hwy, Oakland, MD 21550
    • /65

      Est $237,479

      Not Listed For Sale

      6663 Gorman Rd, Oakland, MD 21550

      • 3 Beds
      • 1.5 Baths
      • 1,982 Sq Ft
      • Built 1978
      6663 Gorman Rd, Oakland, MD 21550

      Last Sold Summary

      • 113 Days On Market

  • /53

    $339,999

    $19K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 990 Sq Ft

    931 Black Oak Dr, Oakland, MD 21550

    Very motivated sellers!!!Escape to Your Profitable Mountain Sanctuary: The Yough Mountain CabinUnveiling the Ultimate Turnkey Retreat & High-Performing InvestmentNestled in the breathtaking heart of the exclusive Yough Mountain Resort, this stunning 3-bedroom cabin offers the perfect harmony of rustic soul and modern investment savvy. Whether you are looking for a private family getaway

    ANGELA BOSLEY Taylor-Made Deep Creek Real Estate, LLC

    931 Black Oak Dr, Oakland, MD 21550
  • /86

    $1,100,000

    Sold Aug 27, 2025

    216 Tarn Dr, Oakland, MD 21550

    • 6 Beds
    • 4.5 Baths
    • 4,769 Sq Ft
    • Built 2020

    Last Sold Summary

    • $231/SF
    • 122 Days On Market

    Current Estimated Value $1,248,275

    Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    216 Tarn Dr, Oakland, MD 21550
    • /83

      Est $349,837

      Not Listed For Sale

      10 Sunset Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,167 Sq Ft
      • Built 1979
      10 Sunset Dr, Oakland, MD 21550

      Last Sold Summary

      • 53 Days On Market

  • /8

    $17,000

    Pending
    • Land
    • 33,541 Sq Ft
    • $22,078 per Acre

    Lot 40 W Big Piney Dr, Oakland, MD 21550

    Located in the Youghiogheny Mountain Resort community, this .77ac lot offers the ultimate gateway to peaceful surroundings, beautiful views, and abundant wildlife. Approved for a sand mound sewage system, this lot provides the perfect opportunity to build your future outdoor enthusiast retreat! Enjoy exclusive access to over 50 miles of private roads and trails perfect for ATV and side-by-side

    Elizabeth Broadwater Taylor-Made Deep Creek Real Estate, LLC

    Lot 40 W Big Piney Dr, Oakland, MD 21550
  • /38

    $265,000

    Sold Dec 30, 2025

    968 Hutton Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 2012

    Last Sold Summary

    • $148/SF
    • 25 Days On Market

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    968 Hutton Rd, Oakland, MD 21550
    • /32

      Est $225,536

      Not Listed For Sale

      601 E Oak St, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 1,744 Sq Ft
      • Built 1922
      601 E Oak St, Oakland, MD 21550

      Last Sold Summary

      • 3 Days On Market

  • /64

    $769,900

    $30K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,780 Sq Ft

    467 Paradise Ridge Rd, Oakland, MD 21550

    Panoramic mountain and lake views set the tone at this lake access home in Paradise Ridge, one of Deep Creek’s most sought-after communities! Perched at the top of the hill on 1.29 acres, this 4-bedroom, 3 full and 1 half bath retreat offers 3,780 finished square feet across three levels. Abundant glass frames the surrounding ridgelines with views of Deep Creek Lake from every room in the house!

    Jon Bell Railey Realty, Inc.

    467 Paradise Ridge Rd, Oakland, MD 21550
  • /21

    $295,000

    Sold Dec 23, 2025

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550

    • 2 Beds
    • 1 Bath
    • 752 Sq Ft
    • Built 1997

    Last Sold Summary

    • $392/SF
    • 21 Days On Market

    Current Estimated Value $297,068

    Last Listing Agent James Matthews Taylor-Made Deep Creek Real Estate, LLC

    157 Jeffrey Ln Unit 21C, Oakland, MD 21550
    • /78

      Est $296,147

      Not Listed For Sale

      3416 Wilson Corona Rd, Oakland, MD 21550

      • 4 Beds
      • 1.5 Baths
      • 1,936 Sq Ft
      • Built 1973
      3416 Wilson Corona Rd, Oakland, MD 21550

      Last Sold Summary

      • 4 Days On Market

  • /113

    $715,000

    Pending
    • 4 Beds
    • 5 Baths
    • 3,240 Sq Ft

    250 Lehman Ln Unit 39, Oakland, MD 21550

    Immaculate 4-bedroom log home in the highly sought after Gallatin Woods community. Custom built with custom finishes throughout. Granite counters, hardwood floors, 2 fireplaces, extensive hardscaped patio and outdoor fireplace, and the list of upgrades literally goes on and is available on request for the discerning buyer. Minutes from Deep Creek Lake and all of the area amenities yet tucked away

    Richard Candy Synergy Realty

    250 Lehman Ln Unit 39, Oakland, MD 21550

Showing Results 361 - 400, Page 10 of 18

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